N-(Cyclopropyl-triazinyl-n&#39;-(arylsulfonyl) ureas having herbicidal activity

ABSTRACT

N-(Cyclopropyl-triazinyl- and -pyrimidinyl)-N&#39;-arylsulfonyl ureas of the formula ##STR1## wherein Ar is a phenyl group ##STR2## or a naphthyl group ##STR3## and Q is a group X-A or R 3 , 
     A is a C 3  -C 6  -alkynyl group, a C 1  -C 6  -alkyl group which is unsubstituted or substituted by halogen, C 1  -C 4  -alkoxy, C 1  -C 4  -alkylthio, C 1  -C 4  -alkylsulfinyl, C 1  -C 4  -alkylsulfonyl, C 1  -C 4  -haloalkoxy, C 1  -C 4  -haloalkylthio, C 1  -C 4  -haloalkylsulfinyl or C 1  -C 4  -haloalkylsulfonyl, or a C 2  -C 6  -alkenyl group which is unsubstituted or substituted by the groups given in the foregoing for C 1  -C 6  -alkyl, or A is a phenyl or benzyl group, 
     E is the methine group or nitrogen, 
     X is oxygen, sulfur, or a sulfinyl or sulfonyl bridge, 
     Z is oxygen or sulfur, 
     R 1  is hydrogen, C 1  -C 4  -alkyl or C 1  -C 4  -alkoxy, 
     R 2  is halogen, C 1  -C 3  -alkyl, C 1  -C 3  -haloalkyl, C 1  -C 3  -alkoxy, C 1  -C 3  -haloalkoxy, amino, C 1  -C 3  -alkylamino, di-(C 1  -C 3  -alkyl)amino, C 3  -C 6  -cycloalkyl or C 2  -C 6  -alkoxyalkyl, 
     R 3  is hydrogen, halogen, C 1  -C 5  -alkyl, C 2  -C 5  -alkenyl, C 1  -C 4  -haloalkyl, or a group --X-R 6 , --COZR 11 , --NO 2  or --CO-NR 8  R 9 , --CN, --COR 10 , --NR 1  R 7  or --NR 1  -COR 12 , 
     R 4  is hydrogen, C 1  -C 4  -alkyl, C 1  -C 4  -alkoxy, C 1  -C 4  -alkylthio, C 1  -C 4  -haloalkyl, C 1  -C 4  -haloalkoxy, halogen, or alkoxyalkyl having at most 4 carbon atoms, 
     R 5  is the same as R 3  but independent thereof, 
     R 6  and R 7  are each C 1  -C 5  -alkyl, C 2  -C 5  -alkenyl or C 2  -C 6  -alkynyl, 
     R 8  and R 9  independently of one another are each hydrogen, C 1  -C 5  -alkyl, C 2  -C 5  -alkenyl or C 2  -C 6  -alkynyl, 
     R 10  is hydrogen, C 1  -C 4  -alkyl or C 1  -C 3  -haloalkyl, 
     R 11  is hydrogen, C 1  -C 4  -alkyl, C 1  -C 3  -haloalkyl, C 3  -C 5  -alkenyl, C 3  -C 5  -alkynyl, phenyl or benzyl, and 
     R 12  is the same as R 1  but independent thereof, and the salts of these compounds with amines, alkali metal bases or alkaline-earth metal bases or with quaternary ammonium bases, have good pre- and post-emergence-selective herbicidal and plant-growth-regulating properties.

The present invention relates to novel, herbicidally effectiveN-(cyclopropyl-triazinyl- and -pyrimidinyl)-N'-(arylsulfonyl) ureas, toprocesses for producing them, to compositions containing them as activeingredients, and to the use thereof for controlling weeds, especiallyselectively, in crops of cultivated plants, or for regulating plantgrowth.

The N-(cyclopropyl-triazinyl- and -pyrimidinyl)-N'-(arylsulfonyl) ureasaccording to the invention correspond to the general formula I ##STR4##wherein Ar is a phenyl group ##STR5## or a naphthyl group ##STR6## and Qis a group X-A or R₃,

A is a C₃ -C₆ -alkynyl group, a C₁ -C₆ -alkyl group which isunsubstituted or substituted by halogen, C₁ -C₄ -alkoxy, C₁ -C₄-alkylthio, C₁ -C₄ -alkylsulfinyl, C₁ -C₄ -alkylsulfonyl, C₁ -C₄-haloalkoxy, C₁ -C₄ -haloalkylthio, C₁ -C₄ -haloalkylsulfinyl or C₁ -C₄-haloalkylsulfonyl, or a C₂ -C₆ -alkenyl group which is unsubstituted orsubstituted by the groups given in the foregoing for C₁ -C₆ -alkyl, or Ais a phenyl or benzyl group,

E is the methine group or nitrogen,

X is oxygen, sulfur, or a sulfinyl or sulfonyl bridge,

Z is oxygen or sulfur,

R₁ is hydrogen, C₁ -C₄ -alkyl or C₁ -C₄ -alkoxy,

R₂ is halogen, C₁ -C₃ -alkyl, C₁ -C₃ -haloalkyl, C₁ -C₃ -alkoxy, C₁ -C₃-haloalkoxy, amino, C₁ -C₃ -alkylamino, di-(C₁ -C₃ -alkyl)amino, C₃ -C₆-cycloalkyl or C₂ -C₆ -alkoxyalkyl,

R₃ is hydrogen, halogen, C₁ -C₅ -alkyl, C₂ -C₅ -alkenyl, C₁ -C₄-haloalkyl, or a group --X--R₆, --COZR₁₁, --NO₂ or --CO--NR₈ R₉, --CN,--COR₁₀, --NR₁ R₇ or --NR₁ --COR₁₂,

R₄ is hydrogen, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₄-haloalkyl, C₁ -C₄ -haloalkoxy, halogen, or alkoxyalkyl having at most 4carbon atoms,

R₅ is the same as R₃ but independent thereof,

R₆ and R₇ are each C₁ -C₅ -alkyl, C₂ -C₅ -alkenyl or C₂ -C₆ -alkynyl,

R₈ and R₉ independently of one another are each hydrogen, C₁ -C₅ -alkyl,C₂ -C₅ -alkenyl or C₂ -C₆ -alkynyl,

R₁₀ is hydrogen, C₁ -C₄ -alkyl or C₁ -C₃ -haloalkyl,

R₁₁ is hydrogen, C₁ -C₄ -alkyl, C₁ -C₃ -haloalkyl, C₃ -C₅ -alkenyl, C₃-C₅ -alkynyl, phenyl or benzyl, and

R₁₂ is the same as R₁ but independent thereof,

and also the salts of these compounds are included.

Urea compounds, triazine compounds and pyrimidine compounds havingherbicidal activity are in general known.Arylsulfamoyl-heterocyclyl-aminocarbamoyl compounds having a herbicidalaction and an action regulating plant growth have recently beendescribed for example in the European Patent Publications Nos. 9419 and10560.

By alkyl in the definitions is meant straight-chain or branched-chainalkyl, for example: methyl, ethyl, n-propyl, i-propyl, the four isomericbutyl groups, n-amyl, i-amyl, 2-amyl, 3-amyl, n-hexyl or i-hexyl.

By alkoxy is meant: methoxy, ethoxy, n-propyloxy, i-propyloxy and thefour isomeric butyl groups, especially however methoxy, ethoxy ori-propoxy.

Examples of alkylthio are: methylthio, ethylthio, n-propylthio,i-propylthio and n-butylthio, particularly however methylthio andethylthio.

Examples of alkenyl groups are: vinyl, allyl, isopropenyl, 1-propenyl,1-butenyl, 2-butenyl, 3-butenyl, 1-isobutenyl, 2-isobutenyl, 1-pentenyl,2-pentenyl, 3-pentenyl and 4-pentenyl, especially vinyl, allyl and4-pentenyl.

Examples of alkylsulfinyl are: methylsulfinyl, ethylsulfinyl,n-propylsulfinyl and n-butylsulfinyl, in particular methylsulfinyl andethylsulfinyl.

Examples of alkylsulfonyl are: methylsulfonyl, ethylsulfonyl,n-propylsulfonyl and n-butylsulfonyl, especially methylsulfonyl andethylsulfonyl.

By halogen in the definitions as well as in haloalkyl, haloalkoxy,haloalkylsulfinyl, haloalkylsulfonyl and haloalkylthio are meantfluorine, chlorine and bromine, preferably however fluorine andchlorine.

Correspondingly, by haloalkyl or by haloalkyl moieties of theabove-defined substituents are meant for example: chloromethyl,fluoromethyl, difluoromethyl, trifluoromethyl, 2-chloroethyl,2,2,2,-trifluoroethyl, 1,1,2,2-tetrafluoroethyl, pentafluoroethyl,1,1,2-trifluoro-2-chloroethyl, 2,2,2-trifluoro-1,1-dichloroethyl,pentachloroethyl, 3,3,3-trifluoropropyl, 2,3-dichloropropyl,1,1,2,3,3,3-hexafluoropropyl, particularly chloromethyl, difluoromethyl,trifluoromethyl and trichloromethyl.

Alkynyl groups in the definitions of the above symbols are as a rule:propargyl, 2-butynyl, 3-butynyl, and also isomeric pentynyl or hexynylgroups; preferably however, the alkynyl group is propargyl or 2- or3-butynyl.

The invention embraces also the salts which the compounds of the formulaI can form with amines, alkali metal and alkaline-earth metal bases orquaternary ammonium bases.

Alkali metal hydroxides and alkaline-earth metal hydroxides to beemphasised as salt formers are hydroxides of lithium, sodium, potassium,magnesium or calcium, especially those of sodium and potassium.

Examples of amines suitable for salt formation are: primary, secondaryand tertiary aliphatic and aromatic amines, such as methylamine,ethylamine, propylamine, i-propylamine, the four isomeric butylamines,dimethylamine, diethylamine, diethanolamine, dipropylamine,diisopropylamine, di-n-butylamine, pyrrolidine, piperidine, morpholine,trimethylamine, triethylamine, tripropylamine, quinuclidine, pyridine,quinoline and i-quinoline, particularly ethyl-, propyl-, diethyl- ortriethylamine, especially iso-propylamine and diethanolamine.

Examples of quaternary ammonium bases are in general the cations ofhaloammonium salts, for example: the tetramethylammonium cation, thetrimethylbenzylammonium cation, the triethylbenzylammonium cation, thetetraethylammonium kation or trimethylethylammonium kation, and also theammonium cation.

Preferred compounds of the formula I according to the invention arethose wherein

Ar is a phenyl group substituted in the ortho-position by Q, E is thenitrogen atom or the methine group, R₁ is hydrogen or methyl, R₂ is a C₁-C₃ -alkyl, C₁ -C₃ -haloalkyl, C₁ -C₃ -alkoxy, C₁ -C₃ -haloalkoxy or C₁-C₃ -alkylamino group, and Z is oxygen.

Ar is a phenyl group substituted in the ortho position by C₁ -C₄-alkoxycarbonyl, E is the nitrogen atom or the methine group, R₁ ishydrogen or methyl, R₂ is a C₁ -C₃ -alkyl, C₁ -C₃ -haloalkyl, C₁ -C₃-alkoxy, C₁ -C₃ -haloalkoxy or C₁ -C₃ -alkylamino group, and Z isoxygen.

Ar is a phenyl group substituted in the ortho position by C₁ -C₃-haloalkoxy, E is the nitrogen atom or the methine group, R₁ is hydrogenor methyl, R₂ is a C₁ -C₃ -alkyl, C₁ -C₃ -haloalkyl, C₁ -C₃ -alkoxy, C₁-C₃ -haloalkoxy or C₁ -C₃ -alkylamino group, and Z is oxygen.

Ar is a phenyl group substituted in the ortho position by halogen ornitro, E is the nitrogen atom or the methine group, R₁ is hydrogen ormethyl, R₂ is a C₁ -C₃ -alkyl, C₁ -C₃ -haloalkyl, C₁ -C₃ -alkoxy, C₁ -C₃-haloalkoxy or C₁ -C₃ -alkylamino group, and Z is oxygen.

Especially preferred are the compounds:

N-(4-cyclopropyl-6-methyl-pyrimidin-2-yl)-N'-(2-methoxycarbonylbenzenesulfonyl)urea,

N-(4-cyclopropyl-6-methoxy-1,3,5-triazin-2-yl)-N'-(2-methoxycarbonylbenzenesulfonyl)urea,

N-(4-cyclopropyl-6-ethoxy-1,3,5-triazin-2-yl)-N'-(2-difluoromethoxybenzenesulfonyl)urea,and

N-(4-cyclopropyl-6-ethoxy-1,3,5-triazin-2-yl)-N'-(2-methoxycarbonylbenzenesulfonyl)urea.

The compounds of the formula I are produced in an inert organic solvent.

According to one process, the compounds of the formula I are produced byreacting a sulfonamide of the formula II

    Ar--SO.sub.2 NH.sub.2                                      (II),

wherein Ar has the meaning defined under the formula I, in the presenceof a base, with an N-pyrimidinyl- or -triazinylcarbamate of the formulaIII ##STR7## wherein E, R₂ and Z have the meanings defined under theformula I, and B--O-- is a phenoxy, phenylalkoxy or alkoxy group whichcan be detached.

According to a second process, compounds of the formula I wherein R ishydrogen are produced by reacting a sulfonylisocyanate orsulfonylisothiocyanate of the formula IV ##STR8## wherein Ar and Zhaving the meanings defined under the formula I, in the presence orabsence of a base, with an amine of the formula V ##STR9## wherein E, R₁and R₂ have the meanings defined under the formula I.

According to a further process, the compounds of the formula I areproduced by reacting a sulfonamide of the formula II given above, in thepresence or absence of a base, with an isocyanate or isothiocyanate ofthe formula VI ##STR10## wherein E, R₂ and Z have the meanings definedunder the formula I.

Furthermore, the compounds of the formula I can be produced by reactingan N-phenylsulfonylcarbamate of the formula VII ##STR11## wherein Ar andB have the meanings defined in the foregoing, with an amine of theformula V given above.

The resulting ureas of the formula I can if required be converted, bymeans of amines, alkali metal hydroxides or alkaline-earth metalhydroxides or quaternary ammonium bases, into addition salts. This iseffected for example by reaction with the equimolar amount of a base,and removal of the solvent by evaporation.

The starting materials of the formulae II, IV and VII are known and canbe produced by known methods.

The cyclopropyl-pyrimidines and cyclopropyltriazines of the formula V,to which the intermediates of the formulae III and VI are stronglyrelated, are in part novel. They and the production thereof likewiseform subject matter of this invention.

2-Amino-4-cyclopropyl-6-methyl-pyrimidine is produced by treatment ofcyclopropanecarboxylic acid or the anhydride thereof, in acetone, withboron trifluoride gas. There is formed cyclopropylbutane-1,3-dione,which is isolated, and then condensed, in an aqueous or alcoholicsolution, with guanidine or with a guanidine salt, corresponding to thereaction pattern ##STR12##

This compound can be reacted directly with an arylsulfonylisocyanate, orit can before the reaction be converted, in a known manner, into anisocyanate or into a carbamic acid ester.

2-Amino-4-cyclopropyl-6-hydroxy-pyrimidine is obtained by reaction of acyclopropylcarboxylic acid halide, for example, the chloride or bromide,with 2,2-dimethyl-4,6-dioxo-dioxane (malonic acid-acetonacetal) in abasic solvent, for example in pyridine. There is formed2,2-dioxane-4,6-dioxy-5-cyclopropylcarbonyldioxane, which is cleaved inwater or in boiling alcohol to give cyclopropyloxo-acetic acid and anester thereof, respectively. The stated compound is reacted withguanidine in water or in a lower alcohol to obtain2-amino-4-cyclopropyl-6-hydroxy-pyrimidine, corresponding to the scheme:##STR13##

The hydroxyl group can be replaced by a halogen atom when this compoundis treated with a halogenating agent, such as phosphorus oxychloride orphosphorus oxybromide. The halogen atom for its part can be replaced ina known manner by other substituents R₂, and the2-amino-4-cyclopropylpyrimidines thus obtained can be reacted directlywith an arylsulfonylisocyanate, or they can before the reaction beconverted in a known manner into an isocyanate or into a carbamic acidester.

2-Amino-4-cyclopropyl-6-trichloromethyl-1,3,5-triazine is produced bycondensing 2 mols of trichloroacetonitrile with one mol ofcyclopropylnitrile in the presence of hydrogen chloride to give4-cyclopropyl-2,6-bis(trichloromethyl)-1,3,5-triazine, and then reactingthis compound with one mol of ammonia or of an amine at temperatures of0°-160° C. under normal pressure, corresponding to the reaction scheme:##STR14##

By reaction either of4-cyclopropyl-2,6-bis-trichloromethyl-1,3,5-triazine or of2-amino-4-cyclopropyl-6-trichloromethyl-1,3,5-triazine, in an absoluteorganic solvent, with at least the molar amount of an alkanol R₂ OH orof the alkali salt thereof, there is obtained the corresponding2-amino-4-cyclopropyl-6-alkoxy-1,3,5-triazines of the formula V or2-cyclopropyl-4,6-bis(alkoxy)-1,3,5-triazines, which can be converted,for example at higher temperatures 40°-140° C. and under pressure, withat least the molar amount of amine to give2-amino-4-cyclopropyl-6-alkoxy-1,3,5-triazine. The2-amino-4-cyclopropyl-1,3,5-triazines thus obtained can be reacteddirectly with an arylsulfonylisocyanate, or they can be converted byreaction in a known manner into an isocyanate or into a carbamic acidester.

2-(γ-Chloropropyl)-4,6-bis-(trichloromethyl)-1,3,5-triazine is obtainedin an analogous manner by condensation of 2 mols oftrichloroacetonitrile and one mol of γ-chlorobutyronitrile in thepresence of hydrogen chloride. This compound can be reacted with themolar amount of amine H₂ NR₁ at 0°-160° C. under normal pressure to give2-amino-4-(γ-chloropropyl)-6-trichloromethyl-1,3,5-triazine, which isconverted with an alkali alcoholate in a suitable solvent at 0°-200° C.into 2-amino-4-cyclopropyl-6-alkoxy-1,3,5-triazine, and then furtherprocessed with an arylsulfonic acid isocyanate or -carbamic acid radicalto obtain the desired urea of the formula I.

These reactions to compounds of the formula I are advantageouslyperformed in aprotic, inert organic solvents, such as methylenechloride, tetrahydrofuran, acetonitrile, dioxane and toluene.

The reaction temperatures are preferably between -20° and +120° C. Thereactions proceed in general slightly exothermically, and can beperformed at room temperature. For the purpose of shortening thereaction time or of initiating the reaction, heat is advantageouslyapplied for a short time up to the boiling point of the reactionmixture. The reaction times can be shortened also by the addition of afew drops of a base or isocyanate as a reaction catalyst.

The final products can be isolated by concentration by evaporationand/or by evaporating off the solvent, and purified by recrystallisationor by trituration of the solid residue in solvents in which they do notreadily dissolve, such as ethers, aromatic hydrocarbons or chlorinatedhydrocarbons.

The active substances of the formula I are stable compounds, and thehandling of them requires no special safety measures.

In low applied amounts, which as a rule are from 0.01 to 1 kg perhectare, the compounds of the formula I are distinguished by goodselective-growth retarding and selective-herbicidal properties, whichrender them excellently suitable for use in crops of cultivated plants,especially in crops of cereals, cotton, soya-bean, colza, maize andrice. It is also possible in some cases to destroy weeds which could bedealt with hitherto only by the application of total herbicides.

The mode of action of these active substances is unusual. Many arecapable of being translocated, that is to say, they are taken up by theplant and transported to other locations, where they produce the desiredeffect. It is thus possible for example by surface treatment ofperennial weeds to destroy them at their roots. The novel compounds ofthe formula I are effective in applied amounts which are very smallcompared with the amounts required to obtain the same effect using otherherbicides and plant-growth regulators.

The compounds of the formula I also have excellent properties forregulating, especially reducing, plant growth. Both monocotyledons anddicotyledons are impaired in their growth.

Thus, for example, the leguminosae frequently planted as cover crops inagriculture in tropical regions can be selectively inhibited in theirgrowth by the compounds of the formula I, the result being that soilerosion between the cultivated plants is prevented, without the covercrops being able to compete with the main cultivated crop.

Furthermore, the compounds of the formula I are suitable for preventingthe sprouting of stored potatoes. Shoots frequently form on potatoesbeing stored during the winter, and the shoots cause shrinkage, loss inweight and rotting.

With larger applied amounts of active substance, all the tested plantswere impaired in their development to the extent that they died.

The invention relates also to herbicidal and plant-growth-regulatingcompositions containing a novel active ingredient of the formula I, andalso to processes for the pre- and post-emergence controlling of weeds,and for the reduction in growth of monocotyledonous and dicotyledonousplants, particularly that of grasses, tropical cover crops and sideshoots of tobacco plants.

The compounds of the formula I are used either in an unmodified form orpreferably in compositions, together with auxiliaries customarilyemployed in formulation practice, and are thus processed, in a knownmanner, for example into the form of emulsion concentrates, directlysprayable or dilutable solutions, diluted emulsions, wettable powders,soluble powders, dusts or granulates, and also encapsulations in forexample polymeric substances. The application processes, such asspraying, atomising, dusting, scattering or pouring, and likewise thetype of compositions, are selected to suit the objects to be achievedand the given conditions.

The formulations, that is to say, the compositions or preparationscontaining the active ingredient of the formula I and optionally a solidor liquid additive, are produced in a known manner, for example by theintimate mixing and/or grinding of the active ingredients withextenders, such as with solvents, solid carriers and optionallysurface-active compounds (tensides).

Suitable solvents are: aromatic hydrocarbons, preferably the fractionsC₈ to C₁₂, such as xylene mixtures or substituted naphthalenes, phthalicesters, such as dibutyl- or dioctylphthalate, aliphatic hydrocarbons,such as cyclohexane or paraffins, alcohols and glycols, as well asethers and esters thereof, such as ethanol, ethylene glycol, ethyleneglycol monomethyl or -ethyl ethers, ketones, such as cyclohexanone,strongly polar solvents, such as N-methyl-2-pyrrolidone,dimethylsulfoxide or dimethylformamide, as well as optionally epoxidisedvegetable oils, such as epoxidised coconut oil or soybean oil; or water.

The solid carriers used, for example for dusts and dispersible powders,are as a rule natural mineral fillers, such as calcite, talcum, kaolin,montmorillonite or attapulgite. In order to improve the physicalproperties, it is also possible to add highly dispersed silicic acid orhighly dispersed absorbent polymers. Suitable granulated adsorptivecarriers are porous types, for example pumice, ground brick, sepioliteor bentonite; and suitable nonsorbent carriers are materials such ascalcite or sand. There can also be used a great number of pre-granulatedmaterials of inorganic or organic nature, such as in particular dolomiteor ground plant residues.

Suitable surface-active compounds are, depending on the nature of theactive substance of the formula I to be formulated, nonionic, cationicand/or anionic tensides having good emulsifying, dispersing and wettingproperties. By `tensides` are also meant mixtures of tensides.

Suitable anionic tensides are both so-called water-soluble soaps as wellas water-soluble, synthetic, surface-active compounds.

Soaps which are applicable are the alkali metal, alkaline-earth metal oroptionally substituted ammonium salts of higher fatty acids (C₁₀ -C₂₂),for example the Na or K salts of oleic or stearic acid, or of naturalfatty acid mixtures, which can be obtained for example from coconut oilor tallow oil. Also to be mentioned are the fatty acid-methyl-taurinesalts.

So-called synthetic tensides are however more frequently used,particularly fatty sulfonates, fatty sulfates, sulfonated benzimidazolederivatives or alkylarylsulfonates. The fatty sulfonates or sulfates areas a rule in the form of alkali metal, alkaline-earth metal oroptionally substituted ammonium salts, and contain an alkyl group having8 to 22 C atoms, `alkyl` including also the alkyl moiety of acyl groups,for example the Na or Ca salts of ligninsulfonic acid, ofdodecylsulfuric acid ester or of a fatty alcohol sulfate mixtureproduced from natural fatty acids. Included among these are also thesalts of sulfuric acid esters and sulfonic acids of fatty alcoholethylene oxide adducts. The sulfonated benzimidazole derivativespreferably contain 2 sulfonic acid groups and a fatty acid group having8-22 C atoms. Alkylarylsulfonates are for example the Na, Ca ortriethanolamine salts of dodecylbenzenesulfonic acid, ofdibutylnaphthalenesulfonic acid or of a naphthalenesulfonicacid-formaldehyde condensation product. Also suitable are correspondingphosphates, for example salts of the phosphoric ester of ap-nonylphenol-(4-14)ethylene oxide adduct.

Suitable nonionic tensides are in particular polyglycol etherderivatives of aliphatic or cycloaliphatic alcohols, saturated orunsaturated fatty acids and alkylphenols, which can contain 3 to 30glycol ether groups and 8 to 20 carbon atoms in the (aliphatic)hydrocarbon radical and 6 to 18 carbon atoms in the alkyl moiety of thealkylphenols.

Further suitable nonionic tensides are the water-soluble polyethyleneoxide adducts, which contain 20 to 250 ethylene glycol ether groups and10 to 100 propylene glycol ether groups, with polypropylene glycol,ethylenediaminopolypropylene glycol and alkylpolypropylene glycol having1 to 10 carbon atoms in the alkyl chain. The compounds mentioned usuallycontain 1 to 5 ethylene glycol units per propylene glycol unit. Examplesof nonionic tensides which may be mentioned are:nonylphenolpolyethoxyethanols, castor oil polyglycol ethers,polypropylene/polyethyleneoxy adducts, tributylphenoxypolyethoxyethanol,polyethylene glycol and octylphenoxypolyethoxyethanol. Suitable also arefatty acid esters of polyoxyethylenesorbitan, such aspolyoxyethylenesorbitan-trioleate.

In the case of the cationic tensides, they are in particular quaternaryammonium salts which contain as N-substituents at least one alkyl grouphaving 8 to 22 C atoms and, as further substituents, lower, optionallyhalogenated alkyl, benzyl or lower hydroxyalkyl groups. The salts arepreferably in the form of halides, methyl sulfates or ethyl sulfates,for example stearyltrimethylammonium chloride orbenzyldi(2-chloroethyl)ethylammonium bromide.

The tensides customarily used in formulation practice are described,inter alia, in the following publications: "Mc Cutcheon's Detergents andEmulsifiers Annual" MC Publishing Corp., Ridgewood, N.J., 1979; andSisley and Wood, "Encyclopedia of Surface Active Agents", ChemicalPublishing Co., Inc. New York, 1964.

The agrochemical preparations contain as a rule 0.1 to 95%, especially0.1 to 80%, of active ingredient of the formula I, 1 to 99.9% of a solidor liquid additive, and 0 to 25%, particularly 0.1 to 25%, of a tenside.

Preferred formulations are made up in particular as follows (%=percentby weight):

    ______________________________________                                         Emulsifiable                                                                 concentrates                                                                  active ingredients:                                                                         1 to 20%,  preferably 5 to 10%                                  surface active agent:                                                                       5 to 30%,  preferably 10 to 20%                                 liquid carrier:                                                                             50 to 94%, preferably 70 to 85%.                                Dusts                                                                         active ingredient:                                                                          0.1 to 10%,                                                                              preferably 0.1 to 1%                                 solid carrier:                                                                              99.9 to 90%,                                                                             preferably 99.9 to 99%.                              Suspension concentrates                                                       active ingredient:                                                                          5 to 75%,  preferably 10 to 50%                                 water:        94 to 25%, preferably 90 to 30%                                 surface-active agent:                                                                       1 to 40%,  preferably 2 to 30%.                                 Wettable powders                                                              active ingredient:                                                                          0.5 to 90%,                                                                              preferably 1 to 80%                                  surface-active agent:                                                                       0.5 to 20%,                                                                              preferably 1 to 15%                                  solid carrier:                                                                              5 to 95%,  preferably 15 to 90%.                                Granulates                                                                    active ingredient:                                                                          0.5 to 30%,                                                                              preferably 3 to 15%                                  solid carrier:                                                                              99.5 to 70%,                                                                             preferably 97 to 85%.                                ______________________________________                                    

Whereas commercial products are preferably in the form of concentratedcompositions, the compositions employed by the end-user are as a rulediluted. The preparations can for application be diluted down to 0.001%of active ingredient. The applied amounts are usually 0.001 to 10 kg,preferably 0.025 to 5, kg of active substance per hectare.

The compositions can also contain additives such as stabilisers,antifoaming agents, viscosity regulators, binders and adhesives, as wellas fertilisers or other active substances for obtaining special effects.

In the following Examples, the temperatures are given in degreesCentigrade (°C.), and pressures in millibars (mb).

EXAMPLE 1 Production of2-cyclopropyl-4,6-bis-trichloromethyl-1,3,5-triazine (intermediate)

760 g of trichloroacetonitrile are cooled to -15° C., and hydrogenchloride gas is blown through the solution until saturation is attained.There are then slowly added, with cooling and introduction of hydrogenchloride gas, 230 g of cyclopropylnitrile in such a manner that thetemperature does not exceed -10° C. The cooling bath is subsequentlyremoved and the reaction mixture is stirred at room temperature untilthe temperature rises to 15° C. There commences from 10° C. upwards,with a moderately exothermic reaction, the splitting-off of hydrogenwhich, after 20 hours' stirring at 15°-20° C., has finally finished.

1.5 liters each of ether and hexane are added to the reaction mixture;the whole is then thoroughly stirred and afterwards filtered. Thefiltrate is concentrated by evaporation; the residue is boiled up in 700ml of hexane, filtration is again performed and the filtrate is oncemore concentrated by evaporation. The residue is recrystallised frommethanol to thus obtain 350 g of the above triazine, m.p. 100°-102° C.

EXAMPLE 2 Production of2-amino-4-cyclopropyl-6-trichloromethyl-1,3,5-triazine

71.2 g of 2-cyclopropyl-4,6-bis-trichloromethyl-1,3,5-triazine aredissolved in 70 ml of tetrahydrofuran, and at room temperature areadded, with stirring, 300 ml of a concentrated aqueous ammonia solution.The reaction mixture is stirred for 30 minutes; it is then diluted withwater, and the formed emulsion is extracted with ether. The ether phasesare collected, dried, filtered and subsequently concentrated byevaporation. The residue crystallises and there remain 48 g of thecrystalline title product, m.p. 111°-114° C.

EXAMPLE 3 Production of2-cyclopropyl-4-methoxy-6-trichloromethyl-1,3,5-triazine

To a solution of 48 g of2-cyclopropyl-4,6-bis-(trichloromethyl)-1,3,5-triazine in 200 ml of MeOHare added, with stirring, 4.9 g of sodium methylate, and the mixture isstirred for 1 hour at room temperature; it is then filtered and thefiltrate is evaporated to dryness. The yield is 28.5 g of the titlecompound as a light-red oil, which solidifies after some time, m.p.49°-51° C.

EXAMPLE 4 Production of 2-cyclopropyl-4,6-dimethoxy-1,3,5-triazine(intermediate)

8.1 g of sodium methylate are added to a solution of 71.2 g of2-cyclopropyl-4,6-bis-(trichloromethyl)-1,3,5-triazine in 200 ml ofmethanol, and stirring is maintained for 5 hours at room temperature.The solution is then evaporated to dryness, and the residue is stirredup with 200 ml of ether. The resulting suspension is filtered and thefiltrate is concentrated by evaporation. The residue crystallises, andis recrystallised from ether/hexane. The yield is 35.7 g of the abovetriazine, m.p. 68°-70° C.

EXAMPLE 5 Production of 2-cyclopropyl-4-amino-6-methoxy-1,3,5-triazine(intermediate)

To a solution of 10.8 g of sodium methylate in 50 ml of methanol areadded 28.9 g of2-amino-4-(3-chloropropyl)-6-trichloromethyl-1,3,5-triazine, and themixture is stirred at 60° C. for 80 minutes. The formed suspension isfiltered under suction, diluted with 250 ml of water, and extracted 3times with 200 ml of ethylene chloride each time. The organic phases aredried, filtered, and concentrated by evaporation. The oil which remainsis purified through a silica gel column, the eluant used being methylenechloride/ether (3:1). The eluant is evaporated off to leave 2.1 g of thetitle product, which is recrystallised from ether/chloroform, m.p.158°-159° C.

EXAMPLE 6 Production of 2-amino-4-cyclopropyl-6-methoxy-1,3,5-triazine(intermediate)

Gaseous ammonia is blown through a solution of 5 g of2-cyclopropyl-4,6-dimethoxy-1,3,5-triazine in 30 ml of methanol at roomtemperature until saturation is reached. The solution is then stirred ina bomb tube (autoclave) at 140° C. for 1 hour; it is subsequentlycooled, and the reaction mixture is filtered to thus obtain 0.5 g of thetitle product as light-brown crystals, m.p. 156°-157° C.

EXAMPLE 7 Production of 2-amino-4-cyclopropyl-6-methoxy-1,3,5-triazine(intermediate)

5 ml of concentrated aqueous ammonia are added to a solution of 1 g of2-cyclopropyl-4-methoxy-6-trichloromethyl-1,3,5-triazine in 3 ml oftetrahydrofuran; the whole is placed into a bomb tube and heated at 80°C. for 30 minutes. The mixture is cooled and then filtered; the filterresidue is dissolved in 30 ml of methylene chloride, and the solution isdried over magnesium sulfate, and concentrated by evaporation. Theresidue crystallises to leave 0.4 g of white crystals, m.p. 157°-158° C.

EXAMPLE 8 Production of2-amino-4-(3-chloropropyl)-6-trichloromethyl-1,3,5-triazine(intermediate)

102.3 g of 2-(3-chloropropyl)-4,6-bis-(trichloromethyl)-1,3,5-triazineare dissolved in 100 ml of tetrahydrofuran, and to this solution areadded, whilst it is being stirred at room temperature, 400 ml ofconcentrated aqueous ammonia solution. After 30 minutes are added 500 mlof water, and the reaction mixture is extracted twice with 100 ml ofether each time. The ether phases are dried over magnesium sulfate,filtered, and concentrated by evaporation to yield 68.3 g of the titleproduct as light-brown oil.

EXAMPLE 9 Production of2-(3-chloropropyl)-4,6-bis-(trichloromethyl)-1,3,5-triazine(intermediate)

Gaseous hydrogen chloride is blown through a solution of 103 g of4-chlorobutyronitrile in 298 g of trichloroacetonitrile at a temperatureof -20° C. until saturation is reached. The mixture is then slowlywarmed to room temperature with stirring, in the course of which only arelatively small evolution of gas results and a crystalline precipitateoccurs. One liter of toluene is added and the reaction mixture isstirred at 85° C. until no further HCl gas evolves. Stirring is thenceased and the mixture is allowed to cool; the clear solution isdecanted from the sludge which has settled. The solution is concentratedby evaporation, and the oil remaining is distilled under high vacuum tothus obtain 294 g of the title compound; b.p. 150°-160° C./0.2 mbar;refractive index n_(D) ²⁷ : 1.5498.

EXAMPLE 10 Production of 2-amino-4-cyclopropyl-6-methoxy-1,3,5-triazine(intermediate)

25.3 g of 2-amino-4-cyclopropyl-6-trichloromethyl-1,3,5-triazine areadded to a solution of 10.8 g of sodium methylate in 50 ml of methanol,and the mixture is stirred at 60° C. for 80 minutes. There are added 300ml of water, and the formed suspension is filtered. The filter residueis suspended twice in 100 ml of acetyl acetate each time, and againfiltered. The organic phases are collected, dried over magnesium sulfateand concentrated by evaporation to thus obtain an oil, whichcrystallises when stirred up in ether. The yield is 6.7 g of the titlecompound, m.p. 158°-159° C.

In a manner analogous to that of these Examples, there are produced thefollowing triazine starting products:

    ______________________________________                                         ##STR15##                                                                      Q         X          Y         Physical data                                ______________________________________                                        CCl.sub.3                                                                             cyclopropyl                                                                              CCl.sub.3   m.p.    Ex. 1                                                                 100-102° C.                             NH.sub.2                                                                              cyclopropyl                                                                              CCl.sub.3   m.p.    Ex. 2                                                                 114-116° C.                             OCH.sub.3                                                                             cyclopropyl                                                                              CCl.sub.3   m.p.    Ex. 3                                                                  49-51° C.                              CH.sub.3                                                                              cyclopropyl                                                                              CH.sub.3    m.p.    Ex. 4                                                                  68-70° C.                              NH.sub.2                                                                              cyclopropyl                                                                              OCH.sub.3   m.p.    Ex. 5,                                                                158-159° C.                                                                    6, 7, 10                               NH.sub.2                                                                              Cl C.sub.3 H.sub.6                                                                       CCl.sub.3   oil     Ex. 8                                  CCl.sub.3                                                                             Cl C.sub.3 H.sub.6                                                                       CCl.sub.3   oil n.sub.D.sup.27 :                                                                  Ex. 9                                                                 1.5498                                         NHC.sub.3 H.sub.7n                                                                    cyclopropyl                                                                              CCl.sub.3   oil                                            NHC.sub.3 H.sub.7n                                                                    cyclopropyl                                                                              NHC.sub.2 H.sub.5                                                                         oil                                            OCH.sub.3                                                                             cyclopropyl                                                                              OH          m.p.                                                                          160- 164° C.                            NHC.sub.3 H.sub.7n                                                                    cyclopropyl                                                                              NH.sub.2    resin                                          OC.sub.2 H.sub.5                                                                      cyclopropyl                                                                              CCl.sub.3   oil                                            NHCH.sub.3                                                                            cyclopropyl                                                                              CCl.sub.3   m.p.                                                                          100-102° C.                             NHC.sub.2 H.sub.5                                                                     cyclopropyl                                                                              CCl.sub.3   m.p.                                                                           47-49° C.                              NHC.sub.3 H.sub.7 iso                                                                 cyclopropyl                                                                              CCl.sub.3   oil                                            N(CH.sub.3).sub.2                                                                     cyclopropyl                                                                              CCl.sub.3   m.p.                                                                           59-61° C.                              NHCH.sub.3                                                                            cyclopropyl                                                                              OCH.sub.3                                                  NHCH.sub.3                                                                            cyclopropyl                                                                              OC.sub.2 H.sub.5                                           NHCH.sub.3                                                                            cyclopropyl                                                                              OCH CF.sub.3                                               NH.sub.2                                                                              cyclopropyl                                                                              OC.sub.2 H.sub.5                                           NH.sub.2                                                                              cyclopropyl                                                                              OCH.sub.2 CF.sub.3                                         NH.sub.2                                                                              cyclopropyl                                                                              OC.sub.2 H.sub.4 Cl                                        NH.sub.2                                                                              cyclopropyl                                                                              OC.sub.2 H.sub.4 OCH.sub.3                                 NH.sub.2                                                                              cyclopropyl                                                                              OCH(CH.sub.3).sub.2                                        NH.sub.2                                                                              cyclopropyl                                                                              SCH.sub.3                                                  NH.sub.2                                                                              cyclopropyl                                                                              NHNHCH.sub.3                                               NH.sub.2                                                                              cyclopropyl                                                                              N(CH.sub.3)NHCH.sub.3                                      NH.sub.2                                                                              cyclopropyl                                                                              NHCOCH.sub.3                                               NH.sub.2                                                                              cyclopropyl                                                                              NH.sub.2                                                   ______________________________________                                    

EXAMPLE 11 Production of 1-cyclopropylbutane-1,3-dione (intermediate)

Boron trifluoride gas is introduced for one hour at 40° C. into amixture of 191 g of cyclopropanecarboxylic acid and 45 g of acetone.There is formed a black oily product, which is diluted with 800 ml ofether. The ether phase is then washed 4 times with 300 ml of water eachtime, and, with ice cooling, 30% sodium hydroxide solution is finallyadded until the pH value is ˜9. The ether layer is separated, and theaqueous phase is extracted three times with 300 ml of ether each time.The ether phases are collected, dried over sodium sulfate, purified withactive charcoal, filtered, and concentrated by evaporation. The oilwhich remains is purified by chromatography through a silica gel columnwith ether/hexane (1:3) as the eluant. The yield after removal of thesolvent by evaporation is 22 g of the title compound as light-colouredoil; refractive index n_(D) ²⁴ : 1.488.

EXAMPLE 12 Production of 2-amino-4-cyclopropyl-6-methylpyrimidine(intermediate)

15 g of guanidine carbonate are added to a mixture of 10 g of1-cyclopropyl-butane-1,3-dione and 150 g of water, and stirring ismaintained at 95° C. for 5 hours. The mixture is then concentrated byevaporation to a volume of 50 ml, and the cooled aqueous concentrate isextracted three times with 100 ml of ethylene chloride each time. Theorganic phase is dried over magnesium sulfate and concentrated byevaporation. The residue crystallises to thus yield 5 g of the titlecompound, m.p. 113°-115° C.

EXAMPLE 13 Production ofN-(4-cyclopropyl-6-methylpyrimidin-2-yl)-N'-(2'-methoxycarbonylbenzenesulfonyl)urea ##STR16##

2.4 g of 2-methoxycarbonyl-benzenesulfonyl-isocyanate are added to amixture of 1 g of 2-amino-4-cyclopropyl-6-methylpyridine in 7 ml ofether and 7 ml of ethylene chloride, and the mixture is stirred for 14hours at room temperature. The occurring precipitate is filtered off tothus obtain 2.2 g of the above urea, m.p. 173°-175° C.

EXAMPLE 14 Production ofN-(4-cyclopropyl-6-methoxy-1,3,5-triazin-2-yl)-N'-(2-methoxycarbonylbenzenesulfonyl)urea##STR17##

2.1 g of 2-methoxycarbonylbenzenesulfonylisocyanate are added withstirring, under a nitrogen atmosphere, to a solution of 1.3 g of2-amino-4-cyclopropyl-6-methoxy-1,3,5-triazine in 10 ml of CH₂ Cl₂. Aslight exothermic reaction occurs, which soon however subsides. Stirringis maintained for 14 hours at room temperature, and the solution is thencaused to crystallise by the addition of ether. The precipitate isfiltered off and dried. The yield is 2.3 g of the above urea, whichmelts at 166°-168° C.

EXAMPLE 15 Production ofN-(4-cyclopropyl-6-trichloromethyl-1,3,5-triazin-2-yl)-N'-(2-difluoromethoxybenzenesulfonyl)urea##STR18##

2.7 g of 2-difluoromethoxybenzenesulfonylisocyanate are added to asolution of 2.54 g of2-amino-4-cyclopropyl-6-trichloromethyl-1,3,5-triazine, and the whole isstirred at room temperature for 14 hours. Hexane is then added until thereaction product precipitates. Filtration is carried out and thefiltration residue is dried to thus obtain 3 g of the above urea, whichmelts at 103°-105° C.

EXAMPLE 16 Production ofN-(4-cyclopropyl-6-methoxy-1,3,5-triazin-2-yl)-N'-(2-difluoromethoxybenzenesulfonyl)urea##STR19##

3.75 g of 2-difluoromethoxybenzenesulfonylisocyanate are added to asolution of 2.5 g of 2-amino-4-cyclopropyl-6-methoxy-1,3,5-triazine in15 ml of methylene chloride, and the mixture is stirred for 70 hours atroom temperature. It is then concentrated by evaporation, and 25 ml ofether are added to the residue. A crystalline precipitate occurs, whichis filtered off. The yield is 4.7 g of the above urea, which melts at121°-124° C.

EXAMPLE 17

The compound of Example 16 can be produced also as follows:

A solution of 0.54 g of NaOCH₃ in 1.26 g of methanol is added to asolution of 0.9 g ofN-(4-cyclopropyl-6-trichloromethyl-1,3,5-triazin-2-yl)-N'-(2-difluoromethoxybenzenesulfonyl)urea(Example 15), and stirring is maintained at 50° C. for one hour. Thereaction mixture is then poured into 100 ml of water; the whole isacidified with 10% aqueous hydrochloric acid to pH 1, and extracted fourtimes with 50 ml of methylene chloride each time. The organic phases aredried over magnesium, filtered, and concentrated by evaporation. Thereremains an oil which, after trituration in ether, crystallises. Thecrystals are recrystallised in ether to thus obtain 0.66 g of the aboveurea, which melts at 122°-124° C.

The following sulfonylureas are produced in a manner analogous to thatof these Examples:

    ______________________________________                                         ##STR20##                                                                                                              Melting                                                                  point                                    No.                                                                             Q      R.sub.1       R.sub.2                                                                            E        (°C.)                             ______________________________________                                        1    COOCH.sub.3   H      OCH.sub.3                                                                              N    166-168°                                                               Example                                                                       14                                    2    COOCH.sub.3   H      CCl.sub.3                                                                              N    162°                                                                   decomp.                               3    Cl            H      OCH.sub.3                                                                              N    161-164°                       4    OCHF.sub.2    H      OCH.sub.3                                                                              N    121-124°                                                               Ex. 16,17                             5    COOCH.sub.3   H      NHC.sub.3 H.sub.7n                                                                     N    187-188°                       6    NO.sub.2      H      OCH.sub.3                                                                              N    179-182°                       7    COOCH.sub.3   H      OC.sub.2 H.sub.5                                                                       N    154-156°                       8    OCH.sub.3     H      OCH.sub.3                                                                              N    142-146°                       9    OCHF.sub.2    H      CCl.sub.3                                                                              N    103-105°                       10   OCHF.sub.2    H      OC.sub.2 H.sub.5                                                                       N    143-144°                       11   NO.sub.2      H      OC.sub.2 H.sub.5                                                                       N    182-184°                       12   OCH.sub.3     H      OC.sub.2 H.sub.5                                                                       N    149-151°                       13   COOCH.sub.3   CH.sub.3                                                                             OCH.sub.3                                                                              N    149-151°                       14   OCHCF.sub.2   CH.sub.3                                                                             OCH.sub.3                                                                              N    118-120°                       15   OCH.sub.3     CH.sub.3                                                                             OCH.sub.3                                                                              N    121-123°                       16   COOCH.sub.3   CH.sub.3                                                                             CCl.sub.3                                                                              N    133-135°                       17   OCHF.sub.2    H      CCl.sub.3                                                                              N    138-140°                                                               Ex. 15                                18   OCHF.sub.2    H      Cl       CH                                         19   COOCH.sub.3   H      CH.sub.3 CH   173-175°                                                               Ex. 13                                20   OCHF.sub.2    H      CH.sub.3 CH   168-169°                       21   OCH.sub.3     H      CH.sub.3 CH   160-162°                       22   NO.sub.2      H      CH.sub.3 CH   153-157°                       23   OCHF.sub.2    H      NHC.sub.3 H.sub.7 iso                                                                  N    233-236°                       24   Cl            H      NHC.sub. 3 H.sub.7 iso                                                                 N    209-211°                       25   OC.sub.2 H.sub.4 OCH.sub.3                                                                  H      OCH.sub.3                                                                              N    130-132°                       26   COOCH.sub.3   H      NHC.sub.3 H.sub.7 iso                                                                  N    210-212°                       27   OCH.sub.3     H      NHC.sub.3 H.sub.7 iso                                                                  N    202-205°                       28   NO.sub.2      H      NHC.sub.3 H.sub.7 iso                                                                  N    211-215°                       29   Cl            H      OH       CH                                         30   NO.sub.2      H      OH       CH                                         31   Cl            H      CH.sub.3 CH                                         32   Cl            H      OCH.sub.3                                                                              CH                                         33   Cl            H      OC.sub.2 H.sub.5                                                                       CH                                         34   OCH.sub.3     H      OCH.sub.3                                                                              CH                                         35   OCH.sub.3     H      OC.sub.2 H.sub.5                                                                       CH                                         36   OCH.sub.3     H      OCH.sub.2 CF.sub.3                                  37   NO.sub.2      H      OCH.sub.3                                                                              CH   201-203°                       38   NO.sub.2      H      OC.sub.2 H.sub.5                                                                       CH                                         39   NO.sub.2      H      OCH.sub.2 CF.sub.3                                                                     CH                                         40   OC.sub.2 H.sub.4 OCH.sub.3                                                                  H      CH.sub.3 CH                                         41   COOCH.sub.3   H      OCH.sub.3                                                                              CH   176-178°                       42   COOCH.sub.3   H      OC.sub.2 H.sub.5                                                                       CH                                         43   COOCH.sub.3   H      OCH.sub.2 CF.sub.3                                                                     N                                          44   COOCH.sub.3   H      OCH.sub.2 CF.sub.3                                                                     CH                                         45   NO.sub.2      H      OCH.sub.2 CF.sub.3                                                                     N                                          46   OCHF.sub.2    H      OCH.sub.2 CF.sub.3                                                                     N -47                                                                              OCHF.sub.2 H OCH.sub.3 CH 170-172.                                            degree.                               48   OCHF.sub.2    H      OC.sub.2 H.sub.5                                                                       CH                                         49   OCHF.sub.2    H      OCH.sub.2 CF.sub.3                                                                     CH                                         50   OC.sub.2 H.sub.4 OCH.sub.3                                                                  H      OC.sub.2 H.sub.5                                                                       N                                          51   OC.sub.2 H.sub.4 OCH.sub.3                                                                  H      OCH.sub.2 CF.sub.3                                                                     N                                          52   OC.sub.2 H.sub.4 OCH.sub.3                                                                  H      CH.sub.3 CH                                         53   OC.sub.2 H.sub.4 OCH.sub.3                                                                  H      OCH.sub.3                                                                              CH   178-181°                       54   OC.sub.2 H.sub.4 OCH.sub.3                                                                  H      OC.sub.2 H.sub.5                                                                       CH                                         55   OC.sub.2 H.sub.4 OCH.sub.3                                                                  H      OCH.sub.2 CF.sub.3                                                                     CH                                         56   SCHF.sub.2    H      OCH.sub.3                                                                              N                                          57   SCHF.sub.2    H      OC.sub.2 H.sub.5                                                                       N                                          58   SCHF.sub.2    H      OCH.sub.2 CF.sub.3                                                                     N                                          59   SCHF.sub.2    H      CH.sub.3 CH                                         60   SCHF.sub.2    H      OCH.sub.3                                                                              CH                                         61   SCHF.sub.2    H      OC.sub.2 H.sub.5                                                                       CH                                         62   SCHF.sub.2    H      OCH.sub.2 CF.sub.3                                                                     CH                                         63   COOCH.sub.3   H      Cl       CH   190-193°                       64   COOCH.sub.3   H      NHC.sub.2 H.sub.5                                                                      N    208-210°                       65   OCHF.sub.2    H      NHC.sub.2 H.sub. 5                                                                     N    230-232°                       66   Cl            H      N(CH.sub.3).sub.2                                                                      N    188-190°                       67   OCHF.sub.2    H      NHCH.sub.3                                                                             N    222-223°                       68   OCHF.sub.2    H      N(CH.sub.3).sub.2                                                                      N    160-162°                       69   COOCH.sub.3   H      N(CH.sub.3).sub.2                                                                      N    153-156°                       70   Cl            H      NHC.sub.2 H.sub.5                                                                      N    227-228°                       71   NO.sub.2      H      NHC.sub.2 H.sub.5                                                                      N    215-217°                       72   Cl            H      SCH.sub.3                                                                              N    120-125°                       73   NO.sub.2      H      Cl       CH   200°                           74   OC.sub.2 H.sub.4 OCH.sub.3                                                                  H      Cl       CH   153-154°                       75   Cl            H      Cl       CH   203-205°                       76   OC(Cl)CHCl    H      Cl       CH   197-200°                       77   OC(Cl)CHCl    H      OCH.sub.3                                                                              CH   212-215°                       78   CO.sub.2 CH.sub.3                                                                           H      CH.sub.3 N    158-160°                       79   COOCH.sub.3   H      OCHF.sub.2                                                                             N    140-142°                       80   COOCH.sub.3   H      C.sub.3 H.sub.5 (cyclo)                                                                CH   178-180°                       81   OCHF.sub.2    H      C.sub.3 H.sub.5 (cyclo)                                                                CH   153-155°                       82   Cl            H      C.sub.3 H.sub.5 (cylco)                                                                CH   215-218°                       83   F             H      C.sub.3 H.sub.5 (cyclo)                                                                CH   194- 197°                      84   CH.sub.3      H      C.sub.3 H.sub.5 (cyclo)                                                                CH   193-197°                       85   OC(Cl)CHCl    H      C.sub.3 H.sub.5 (cyclo)                                                                CH   214-215°                       86   OCHF.sub.2    H      CH.sub.3 N    152-153°                       87   Cl            H      CH.sub.3 N    155-157°                       88   F             H      CH.sub.3 N    159-161°                       89   OC.sub.2 H.sub.4 Cl                                                                         H      CH.sub.3 N    163-165°                       90   OC(Cl)CHCl    H      CH.sub.3 N    172-174°                       91   SCHF.sub.2    H      CH.sub.3 N    178-180°                       92   COOCH.sub.3   H      C.sub.3 H.sub.5 (cyclo)                                                                N    186-188°                       93   OCHF.sub.2    H      C.sub.3 H.sub.5 (cyclo)                                                                N    120-125°                       94   Cl            H      C.sub.3 H.sub.5 (cyclo)                                                                N    195-197°                       95   F             H      C.sub.3 H.sub.5 (cyclo)                                                                N    174-176°                       96   OCH.sub.2 CH.sub.2 Cl                                                                       H      C.sub.3 H.sub.5 (cyclo)                                                                N    178-180°                       97   O(Cl)CHCl     H      C.sub.3 H.sub.5 (cyclo)                                                                N    206-209°                       98   SCHF.sub.2    H      C.sub.3 H.sub.5 (cyclo)                                                                N    165-168°                       99   OCHF.sub.2    H      CH.sub.2 OCH.sub.3                                                                     N    109-112°                       100  Cl            H      CH.sub.2 OCH.sub.3                                                                     N    172-175°                       101  F             H      CH.sub.2 OCH.sub.3                                                                     N    132-136°                       102  OCH.sub.2 CH.sub.2 Cl                                                                       H      CH.sub.2 OCH.sub.3                                                                     N    142-146°                       103  OC.sub.2 H.sub.4 OCH.sub.3                                                                  H      CH.sub.2 OCH.sub.3                                                                     N    129-132°                       104  COOCH.sub.3   H      C.sub.2 H.sub.5                                                                        N    168-170°                       105  OCHF.sub.2    H      C.sub.2 H.sub.5                                                                        N    106-109°                       106  Cl            H      C.sub.2 H.sub.5                                                                        N    190-193°                       107  F             H      C.sub.2 H.sub.5                                                                        N    156-158°                       108  OCH.sub.2 CH.sub.2 Cl                                                                       H      C.sub.2 H.sub.5                                                                        N    163-167°                       109  OCH.sub.2 CH.sub.2 Cl                                                                       H      C.sub.2 H.sub.5                                                                        N    136-138°                       110  SCHF.sub.2    H      OCH.sub.3                                                                              N    163-165°                       111  OC.sub.2 H.sub.4 Cl                                                                         H      OCH.sub.3                                                                              N    155-158°                       112  Cl            H      OC.sub.2 H.sub.5                                                                       N    139-142°                       113  OCH.sub.2 CH.sub.2 Cl                                                                       H      OC.sub.2 H.sub.5                                                                       N    152-155°                       114  OCH.sub.2 CH.sub.2 OCH.sub.3                                                                H      OC.sub.2 H.sub.5                                                                       N    132-135°                       115  SCHF.sub.2    H      OC.sub.2 H.sub.5                                                                       N    163-166°                       116  COOCH.sub.3   H      OC.sub.2 H.sub.5                                                                       N    136-139°                       117  COOCH.sub.3   H      SCH.sub.3                                                                              CH                                         118  COOCH.sub.3   H      OC.sub.2 H.sub.5                                                                       CH                                         119  OCF.sub.3     H      OCH.sub.3                                                                              N                                          120  OCF.sub.3     H      OC.sub.2 H.sub.5                                                                       N                                          121  OCHF.sub.2    H      SCH.sub.3                                                                              CH                                         122  NO.sub.2      H      SCH.sub.3                                                                              CH                                         123  OCH.sub.2 CH.sub.2 Cl                                                                       H      SCH.sub.3                                                                              CH                                         124  OCH.sub.2 CH.sub.2 Cl                                                                       H      SCH.sub.3                                                                              CH                                         125  OC(Cl)CHCl    H      SCH.sub.3                                                                              CH                                         126  SCH.sub.2 OCH.sub.3                                                                         H      OCH.sub.3                                                                              N                                          127  SCH.sub.2 OCH.sub.3                                                                         H      OC.sub.2 H.sub.5                                                                       N                                          128  SCH.sub.2 CHCH.sub.2                                                                        H      OCH.sub.3                                                                              N                                          129  SCH.sub.2 CHCH.sub.2                                                                        H      OC.sub.2 H.sub.5                                                                       N                                          130  SCH.sub.2 CHCH.sub.2                                                                        H      OCH.sub.3                                                                              CH                                         131  SCH.sub.2 CHCH.sub.2                                                                        H      OC.sub.2 H.sub.5                                                                       CH                                         132  SCH.sub.2 OCH.sub.3                                                                         H      OCH.sub.3                                                                              CH                                         133  SCH.sub.2 OCH.sub.3                                                                         H      OC.sub.2 H.sub.5                                                                       CH                                         134  SCH.sub.2 CCH H      OCH.sub.3                                                                              N                                          135  SCH.sub.2 CCH H      OC.sub.2 H.sub.5                                                                       N                                          136  SCH.sub.2 CCH H      OCH.sub.3                                                                              CH                                         137  S(O)CH.sub.2 CCH                                                                            H      OCH.sub.3                                                                              N                                          138  S(O)CH.sub.2CCH                                                                             H      OCH.sub.3                                                                              CH                                         139  SO.sub.2 CH.sub.2 CCH                                                                       H      OCH.sub.3                                                                              N                                          140  SO.sub.2 CH.sub.2 CCH                                                                       H      OCH.sub.3                                                                              CH                                         141  S(O)CH.sub.2 CHCH                                                                           H      OCH.sub.3                                                                              N                                          142  OCH.sub.2 CHCH.sub.2                                                                        H      OCH.sub.3                                                                              N                                          143  OCH.sub.2 CCH H      OCH.sub.3                                                                              N                                          144  NHCOCH.sub.3  H      OCH.sub.3                                                                              N                                          145  CON(CH.sub.3).sub.2                                                                         H      OCH.sub.3                                                                              N                                          146  SO.sub.2 CH.sub.2 C.sub.6 H.sub.5                                                           H      OCH.sub.3                                                                              N                                          147  SO.sub.2 CH.sub.2 C.sub.6 H.sub.5                                                           H      OCH.sub.3                                                                              CH                                         148  SO.sub.2 CH.sub.2 C.sub.6 H.sub.5                                                           H      OC.sub.2 H.sub.5                                                                       CH                                         149  SO.sub.2 CH.sub.2 C.sub.6 H.sub.5                                                           H      OC.sub.2 H.sub.5                                                                       N                                          ______________________________________                                    

FORMULATION EXAMPLES EXAMPLE 18

    ______________________________________                                        Formulation Examples for active ingredients of the formula I                  (% = percent by weight)                                                       (a) Wettable powder                                                                              (a)      (b)     (c)                                       ______________________________________                                        active ingredient  20%      60%     0.5%                                      sodium lignin sulfonate                                                                          5%       5%      5%                                        sodium lauryl sulfate                                                                            3%       --      --                                        sodium diisobutylnaphthalene                                                                     --       6%      6%                                        sulfonate                                                                     octylphenolpolyethylene glycol                                                                   --       2%      2%                                        ether (7-8 mols of ethylene oxide)                                            highly dispersed silicic acid                                                                    5%       27%     27%                                       kaolin             67%      --      --                                        sodium chloride    --       --      59.5%                                     ______________________________________                                    

The active ingredient is well mixed with the additives and ground in asuitable mill. There are obtained wettable powders which can be dilutedwith water to give suspensions of the concentration desired.

    ______________________________________                                        (b) Emulsion concentrate                                                                             (a)    (b)                                             ______________________________________                                        active ingredient      10%    1%                                              octylphenolpolyethylene glycol ether                                                                  3%    3%                                              (4-5 mols of ethylene oxide)                                                  calcium dodecyl benzene sulfonate                                                                     3%    3%                                              castor oil polyglycol ether                                                                           4%    4%                                              (36 mols of ethylene oxide)                                                   cyclohexanone          30%    10%                                             xylene mixture         50%    79%                                             ______________________________________                                    

Emulsions of the concentration desired can be obtained from thisconcentrate by dilution with water.

    ______________________________________                                        (c) Dust          (a)     (b)                                                 ______________________________________                                        active ingredient  0.1%    1%                                                 talcum            99.9%   --                                                  kaolin            --      99%                                                 ______________________________________                                    

Dusts ready for use are obtained by mixing the active-ingredient withthe carriers, and grinding the mixture in a suitable mill.

    ______________________________________                                        (d) Extruder granulate                                                                            (a)    (b)                                                ______________________________________                                        active ingredient   10%    1%                                                 sodium lignin sulfonate                                                                            2%    2%                                                 carboxymethylcellulose                                                                             1%    1%                                                 kaolin              87%    96%                                                ______________________________________                                    

The active ingredient is mixed with the additives, and the mixture isthen ground and moistened with water. It is extruded and subsequentlydried in a stream of air.

    ______________________________________                                        (e) Coated granulate                                                          ______________________________________                                        active ingredient    3%                                                       polyethylene glycol (MG 200)                                                                       3%                                                       kaolin               94%                                                      ______________________________________                                    

The finely ground active ingredient is uniformuly applied, in a mixer,to the kaolin moistened with polyethylene glycol. Non-dusty coatedgranulates are obtained in this manner.

    ______________________________________                                        (f) Suspension concentrate                                                                          (a)     (b)                                             ______________________________________                                        active ingredient     40%     5%                                              ethylene glycol       10%     10%                                             nonylphenolpolyethylene glycol                                                                       6%     1%                                              ether (15 mols of ethylene oxide)                                             sodium lignin sulfonate                                                                             10%     5%                                              carboxymethylcellulose                                                                               1%     1%                                              37% aqueous formaldehyde solution                                                                   0.2%    0.2%                                            silicone oil in the form of a                                                                       0.8%    0.8%                                            75% aqueous emulsion                                                          water                 32%     77%                                             ______________________________________                                    

The finely ground active ingredient is intimately mixed with theadditives. There is thus obtained a suspension concentrate from whichcan be produced, by dilution with water, suspensions of theconcentration required.

    ______________________________________                                        (g) Salt solution                                                             ______________________________________                                        active ingredient      5%                                                     isopropylamine         1%                                                     octylphenolpolyethylene glycol ether                                                                 3%                                                     (78 mols of ethylene oxide)                                                   water                  91%                                                    ______________________________________                                    

Biological Examples EXAMPLE 19 Herbicidal action before emergence of theplants

Plant seeds are sown in flower pots (12-15 cm diameter) in a greenhouse.Th surface of the soil is treated immediately afterwards with an aqueousdispersion or solution of the active ingredients, the concentrationsused being 500 g and 250 g, respectively, of active ingredient perhectare. The pots are then kept in the greenhouse at a temperature of22°-25° C. with 50-70% relative humidity, and the test results areevaluated after 3 weeks. The condition of the plants is assessedaccording to the following scale of ratings:

9 plant has flourished as in the case of the untreated control plant, nodamage,

8 very slight phytotoxic symptoms,

7 slight damage,

6 regenerable damage,

5 permanent damage,

4 stunted growth of plant,

3 severe damage,

2 very severe damage,

1 plant has died or has not germinated.

A selective herbicidal action exists where, with the same appliedamount, the cultivated plant has ratings of 6-9 and the weeds haveratings of 1-4.

The results are summarised in the following.

    __________________________________________________________________________    Compound No.                                                                              1     4     6     10    13    37                                  Applied amount g/ha                                                                       500                                                                              250                                                                              500                                                                              250                                                                              500                                                                              250                                                                              500                                                                              250                                                                              500                                                                              350                                                                              500                                                                              350                              __________________________________________________________________________    plant                                                                         wheat       9  9  7  8  8  8  7  8  6  8  8  8                                Alopecurus myosuroides                                                                    2  3  2  2  3  4  1  3  1  1  2  4                                Echinochloa crus galli                                                                    3  4  4  4  4  4  3  4  1  2  2  2                                Cyperus esculentus                                                                        3  4  3  4  3  4  2  3  1  1  1  1                                Abutilon sp.                                                                              1  2  2  2  3  3  1  2  1  1  2  3                                Xanthium spinosum                                                                         2  3  1  3  3  4  3  4  2  2  2  3                                Chenopodium album                                                                         2  2  1  1  2  2  2  2  2  2  2  2                                Ipomoea purpurea                                                                          2  2  2  3  2  2  2  2  2  2  2  2                                Sinapis alba                                                                              1  1  2  2  2  2  2  2  2  2  2  2                                Galium aparine                                                                            4  4  2  2  1  2  2  3  3  4  2  3                                Viola tricolor                                                                            3  3  2  2  1  1  2  2  1  1  2  2                                __________________________________________________________________________

EXAMPLE 20 Herbicidal action after emergence of the plants (contactaction)

A number of weeds and cultivated plants, both monocotyledons anddicotyledons, are sprayed in the 4- to 6-leaf stage with an aqueousactive-ingredient dispersion in dosages of 4 kg of active substances perhectate, and are then kept at 24° to 26° C. with 45-60% relativehumidity. The test results are evaluated 15 days after the treatment,and the state of the plants is assessed according to the scale ofratings used in the pre-emergence test.

The results are summarised in the following.

    __________________________________________________________________________    Compound No.                                                                              1     3     4     6     7     8                                   Applied amount g/ha                                                                       250                                                                              125                                                                              250                                                                              125                                                                              250                                                                              125                                                                              250                                                                              125                                                                              250                                                                              125                                                                              250                                                                              125                              __________________________________________________________________________    plant                                                                         wheat       9  9  9  9  8  9  9  9  7  8  8  9                                maize       5  7  8  8  7  9  5  7  2  3  5  7                                Alopecurus myosuroides                                                                    4  4  5  7  3  4  4  6  2  3  4  6                                Echinochloa crus galli                                                                    8  8  8  9  8  9  7  8  4  4  2  6                                Cyperus esculentus                                                                        4  4  3  4  3  3  3  4  3  3  4  6                                Abutilon sp.                                                                              2  2  5  5  3  3  3  4  2  3  2  3                                Xanthium spinosum                                                                         1  1  2  2  2  2  2  3  2  2  1  4                                Chenopodium album                                                                         2  2  3  3  2  2  2  3  2  2  2  3                                Ipomoea purpurea                                                                          4  4  3  4  3  4  3  4  3  4  3  5                                Sinapis alba                                                                              2  3  2  3  2  2  2  2  2  2  2  3                                Galium aparine                                                                            2  2  3  3  2  2  2  2  2  2  2  3                                Viola tricolor                                                                            2  4  3  3  2  2  2  2  2  2  3  4                                __________________________________________________________________________

    ______________________________________                                               Verbindung No.                                                                10      19        41        73                                                Aufwandmenge g/ha                                                             250  125    250    125  250  125  250  125                             ______________________________________                                        Pflanze                                                                       Weizen   9      9      3    4    5    7    6    8                             Mais     5      7      3    8    4    8    4    8                             Alopecurus                                                                             2      3      3    4    2    2    3    5                             myosuroides                                                                   Echinochloa                                                                            4      6      2    3    4    5    3    4                             crus galli                                                                    Cyperus  3      5      3    4    3    4    4    5                             esculentus                                                                    Abutilon sp.                                                                           3      3      3    4    2    2    2    3                             Xanthium 2      4      3    3    1    1    2    2                             spinosa                                                                       Chenopodium                                                                            2      3      3    4    2    3    2    2                             album                                                                         Ipomoea  4      4      4    4    4    5    4    4                             purpurea                                                                      Sinapis  2      3      3    3    3    4    3    3                             alba                                                                          Galium   3      4      4    4    3    4    3    5                             aparine                                                                       Viola tricolor                                                                         3      4      4    5    2    3    2    3                             ______________________________________                                    

EXAMPLE 21 Reduction of sprouting on stored potatoes

A number of commercially available potatoes of the "Urgenta" variety,exhibiting no germination (sprouting), are washed and dried. Thepotatoes are afterwards each immersed for one minute inactive-ingredient emulsions of varying concentration; they are then laidout on filter paper in plastics dishes, and stored at temperatures of14° and 21° C. in darkness with 50% relative humidity, and an evaluationis made 34 days after application. At the same time the loss in weightof the tubers and the weight of the sprouts, compared with those valuesin the case of the untreated control specimens are determined. Thecompounds according to the invention brought about in this test acomplete prevention of sprouting. The loss in weight of the potatoes wasless than 10% of that of the control potatoes.

EXAMPLE 22 Reduction in growth of tropical leguminous cover crops

The test plants (centrosema plumieri and centrosema pubescens) arecultivated up to the fully grown stage, and then cut back to a height of60 cm. After 7 days, the active substance is sprayed on in the form ofan aqueous emulsion. The test plants are maintained at 70% relativehumidity and with 6000 lux of artificial light, 14 hours per day, attemperatures of 27° C. by day and 21° C. by night. The test results areassessed 4 weeks after application of the emulsion. The new growthoccurring compared with that on the control plants is estimated andweighed, and the phytotoxicity is evaluated. The plants treated with theactive ingredients of the formula I show in this test a clear reductionin new growth (less than 20% of the new growth occurring on untreatedcontrol plants), without the test plants having suffered damage.

What is claimed is:
 1. AnN-(cyclopropyl-triazinyl-)-N'-(arylsulfonyl)urea of the formula I##STR21## wherein Ar is a phenyl group ##STR22## or a naphthyl group##STR23## and Q is a group X-A or R₃,A is a C₃ -C₆ -alkynyl group, a C₁-C₆ -alkyl group which is unsubstituted or substituted by halogen, C₁-C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulfinyl, C₁ -C₄-alkylsulfonyl, C₁ -C₄ -haloalkoxy, C₁ -C₄ -haloalkylthio, C₁ -C₄-haloalkylsulfinyl or C₁ -C₄ -haloalkylsulfonyl, or a C₂ -C₆ -alkenylgroup which is unsubstituted or substituted by the groups given in theforegoing for C₁ -C₆ -alkyl, or A is a phenyl or benzyl group, X isoxygen, sulfur, or a sulfinyl or sulfonyl bridge, Z is oxygen or sulfur,R₁ is hydrogen, C₁ -C₄ -alkyl or C₁ -C₄ -alkoxy, R₂ is halogen, C₁ -C₃-alkyl, C₁ -C₃ -haloalkyl, C₁ -C₃ -alkoxy, C₁ -C₃ -haloalkoxy, amino, C₁-C₃ -alkylamino, di-(C₁ -C₃ -alkyl)amino, C₃ -C₆ -cycloalkyl or C₂ -C₆-alkoxyalkyl, R₃ is hydrogen, halogen, C₁ -C₅ -alkyl, C₂ -C₅ -alkenyl,C₁ -C₄ -haloalkyl, or a group --X--R₆, --COZR₁₁, --NO₂ or --CO--NR₈ R₉,--CN, --COR₁₀, --NR₁ R₇ or --NR₁ --COR₁₂, R₄ is hydrogen; C₁ -C₄ -alkyl,C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -haloalkyl, C₁ -C₄-haloalkoxy, halogen, or alkoxyalkyl having at most 4 carbon atoms, R₅is the same as R₃ but independent thereof, R₆ and R₇ are each C₁ -C₅-alkyl, C₂ -C₅ -alkenyl or C₂ -C₆ -alkynyl, R₈ and R₉ independently ofone another are each hydrogen, C₁ -C₅ -alkyl, C₂ -C₅ -alkenyl or C₂ -C₆-alkynyl, R₁₀ is hydrogen, C₁ -C₄ -alkyl or C₁ -C₃ -haloalkyl, R₁₁ ishydrogen, C₁ -C₄ -alkyl, C₁ -C₃ -haloalkyl, C₃ -C₅ -alkenyl, C₃ -C₅-alkynyl, phenyl or benzyl, and R₁₂ is the same as R₁ but independentthereof.
 2. A compound according to claim 1, wherein Z is oxygen.
 3. Acompound of the formula I according to claim 2, wherein Ar is a phenylgroup substituted in the orthoposition by Q, R₁ is hydrogen or methyl,and R₂ is a C₁ -C₃ -alkyl, C₁ -C₃ -haloalkyl, C₁ -C₃ -alkoxy, C₁ -C₃-haloalkoxy or C₁ -C₃ -alkylamino group.
 4. A compound of the formula Iaccording to claim 3, wherein Ar is a phenyl group substituted in theorthoposition by C₁ -C₄ -alkoxycarbonyl.
 5. A compound of the formula Iaccording to claim 3, wherein Ar is a phenyl group substituted in theorthoposition by C₁ -C₃ -haloalkoxy.
 6. A compound of the formula Iaccording to claim 3, wherein Ar is a phenyl group substituted in theorthoposition by halogen or nitro. 7.N-(4-Cyclopropyl-6-methoxy-1,3,5-triazin-2-yl)-N'-(2-methoxycarbonylbenzenesulfonyl)ureaaccording to claim
 4. 8.N-(4-Cyclopropyl-6-ethoxy-1,3,5-triazin-2-yl)-N'-(2-difluoromethoxybenzenesulfonyl)ureaaccording to claim
 5. 9. A herbicidal and plant-growth-reducingcomposition which contains, as active ingredient, an effective amount ofan N-phenylsulfonyl-N'-triazinyl-urea according to claim 1, togetherwith a carrier.
 10. A method of controlling undesirable plant growth,which method comprises applying thereto or to the locus thereof aneffective amount of an N-(cyclopropyl-triazinyl)-N'-(arylsulfonyl)-ureaaccording to claim
 1. 11. A method of reducing plant growth, whichmethod comprises applying thereto or to the locus thereof an effectiveamount of an N-(cyclopropyl-triazinyl)-N'-(arylsulfonyl)-urea accordingto claim
 1. 12. A method for the pre- or post-emergence controlling ofweeds in crops of cultivated plants, which method comprises applyingthereto or to the locus thereof an effective amount of anN-(cyclopropyl-triazinyl)-N'-(arylsulfonyl)-urea according to claim 1.13. A method of suppressing plant growth beyond the two-leaf stage,which method comprises applying before emergence of the plants aneffective amount of an N-(cyclopropyl-triazinyl)-N'-(arylsulfonyl)-ureaaccording to claim 1.